Woods made his first major appearance on Khalifa's 2011 song "Taylor Gang," which received gold certification by the Recording Industry Association of America (RIAA).

[8][9] In February 2011, Wiz Khalifa released his ninth mixtape, Cabin Fever, which featured Woods on three tracks, including "Taylor Gang", "Middle of You" and "Homicide".

[10] Woods released his fourth mixtape Red Cup Music, which featured guest appearances by Juicy J, French Montana, and production by ID Labs and Mac Miller in March 2011.

The Cookout mixtape, produced by ID Labs, Sledgren, Cardo, Key Wane and Big Jerm, was released in September 2011 and featured Wiz Khalifa on eight of the eleven tracks.

Labs, Cardo, Sonny Digital, Key Wane, Sledgren and Harry Fraud, was released in June 2012 and featured Taylor Gang's Wiz Khalifa, Lola Monroe, Juicy J, Tuki Carter, as well as artists Soulja Boy, Trae Tha Truth, and Young Jerz.

[22] In a XXL review of Gangland, the magazine stated, "Over the past two years, Taylor Gang's Chevy Woods has gradually built up his name with mixtapes like Red Cup Music and The Cookout.

[24] Woods went on the first Under the Influence of Music concert tour with Khalifa, Mac Miller, Schoolboy Q and Kendrick Lamar in support of Gangland in July and August 2012, .

[28] In August 2013, Woods told HotNewHipHop, his debut album would contain production by Sledgren and C4, the track list for Gangland 2 was finalized, and it would be hosted by DJ Drama.

[30] Woods released Gangland 2, a mixtape featuring guest appearances from Wiz Khalifa, Juicy J, Trinidad James, Young Scooter, King Los and Compton Menace, via Taylor Gang Records in October 2013.

[34] In January 2015, Woods released the third installment of his Gangland series featuring production from Ricky P, Zaytoven, Sonny Digital, Ty Dolla Sign and more.

On October 11, 2016 Taylor Gang Records released a compilation mixtape titled TGOD Volume 1 with all the members including Wiz Khalifa, Berner, Juicy J, Ty Dolla $ign among others.

On November 11, 2016, Gang Sh*t Only was released with features from Wiz Khalifa, Hardo, Stevie B, FTR Drama and Rich The Kid with production Honorable C.N.O.T.E., 808 Mafia, K.E.

On June 15, 2018, Chevy Woods released the mixtape titled 81 with a feature from Wiz Khalifa on the track Bitch You Lyin and production from K.E.